#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:36:10 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230203 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/72/7057268.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7057268
loop_
_publ_author_name
'Jiang, Liang'
'Gao, Hu'
'Gai, Lizhi'
'Shen, Zhen'
_publ_section_title
;
 J-Aggregation induced emission enhancement of a thienyl substituted
 bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY)
 dye
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8271
_journal_paper_doi               10.1039/C8NJ00031J
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C26 H24 B2 F4 N4'
_chemical_formula_weight         490.11
_chemical_name_systematic        2,7-diphenyl-1,3,6,8-tetramethylBOPHY
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-11-24 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.775(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4590(5)
_cell_length_b                   32.400(2)
_cell_length_c                   8.9587(5)
_cell_measurement_reflns_used    5004
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.51
_cell_volume                     2295.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20473
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.512
_exptl_absorpt_coefficient_mu    0.107
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0713P)²+0.9206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3575
_reflns_number_total             5275
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00031j2.cif
_cod_data_source_block           20171025SZ_0m_a
_cod_depositor_comments
'Adding full bibliography for 7057268--7057269.cif.'
_cod_database_code               7057268
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
B1 B 0.9465(3) 0.44153(8) 1.0628(3) 0.0203(5) Uani 1 1 d . .
B2 B 0.4948(3) 0.48964(8) 0.7706(3) 0.0208(5) Uani 1 1 d . .
C1 C 0.7693(3) 0.35118(8) 0.4136(3) 0.0268(5) Uani 1 1 d . .
H1 H 0.738282 0.377815 0.368328 0.032 Uiso 1 1 calc R U
C2 C 0.7324(3) 0.31671(8) 0.3155(3) 0.0332(6) Uani 1 1 d . .
H2 H 0.676961 0.320029 0.203644 0.040 Uiso 1 1 calc R U
C3 C 0.7750(3) 0.27766(8) 0.3782(3) 0.0353(6) Uani 1 1 d . .
H3 H 0.747836 0.254188 0.310274 0.042 Uiso 1 1 calc R U
C4 C 0.8579(3) 0.27296(8) 0.5413(3) 0.0327(6) Uani 1 1 d . .
H4 H 0.888038 0.246198 0.585633 0.039 Uiso 1 1 calc R U
C5 C 0.8967(3) 0.30740(7) 0.6397(3) 0.0272(5) Uani 1 1 d . .
H5 H 0.955134 0.303924 0.751049 0.033 Uiso 1 1 calc R U
C6 C 0.8517(3) 0.34711(7) 0.5785(3) 0.0225(5) Uani 1 1 d . .
C7 C 0.8926(3) 0.38383(7) 0.6845(3) 0.0215(5) Uani 1 1 d . .
C8 C 0.8748(3) 0.38651(7) 0.8361(3) 0.0198(5) Uani 1 1 d . .
C9 C 0.8172(3) 0.35469(7) 0.9262(3) 0.0270(5) Uani 1 1 d . .
H9A H 0.915859 0.340976 1.003141 0.041 Uiso 1 1 calc R U
H9B H 0.746816 0.334216 0.851439 0.041 Uiso 1 1 calc R U
H9C H 0.751210 0.367984 0.983221 0.041 Uiso 1 1 calc R U
C10 C 0.9533(3) 0.42192(7) 0.6554(2) 0.0196(5) Uani 1 1 d . .
C11 C 0.9922(3) 0.43547(7) 0.5118(3) 0.0239(5) Uani 1 1 d . .
H11A H 1.029638 0.411656 0.465631 0.036 Uiso 1 1 calc R U
H11B H 1.081881 0.456327 0.543805 0.036 Uiso 1 1 calc R U
H11C H 0.890305 0.447281 0.432365 0.036 Uiso 1 1 calc R U
C12 C 0.9706(3) 0.44692(7) 0.7880(2) 0.0186(5) Uani 1 1 d . .
C13 C 1.0183(3) 0.48777(7) 0.8154(2) 0.0205(5) Uani 1 1 d . .
H13 H 1.050503 0.501302 0.736511 0.025 Uiso 1 1 calc R U
C14 C 0.2435(3) 0.33888(7) 0.4645(3) 0.0271(5) Uani 1 1 d . .
H14 H 0.205090 0.364319 0.411221 0.033 Uiso 1 1 calc R U
C15 C 0.2047(3) 0.30237(8) 0.3794(3) 0.0336(6) Uani 1 1 d . .
H15 H 0.140441 0.302935 0.268292 0.040 Uiso 1 1 calc R U
C16 C 0.2586(3) 0.26516(8) 0.4547(3) 0.0343(6) Uani 1 1 d . .
H16 H 0.230370 0.240109 0.396068 0.041 Uiso 1 1 calc R U
C17 C 0.3538(3) 0.26443(7) 0.6156(3) 0.0311(6) Uani 1 1 d . .
H17 H 0.392046 0.238841 0.667674 0.037 Uiso 1 1 calc R U
C18 C 0.3938(3) 0.30107(7) 0.7019(3) 0.0259(5) Uani 1 1 d . .
H18 H 0.459649 0.300253 0.812537 0.031 Uiso 1 1 calc R U
C19 C 0.3387(3) 0.33889(7) 0.6283(3) 0.0223(5) Uani 1 1 d . .
C20 C 0.3790(3) 0.37788(7) 0.7195(3) 0.0203(5) Uani 1 1 d . .
C21 C 0.4346(3) 0.41458(7) 0.6684(3) 0.0200(5) Uani 1 1 d . .
C22 C 0.4672(3) 0.42273(7) 0.5177(3) 0.0257(5) Uani 1 1 d . .
H22A H 0.367685 0.435896 0.439841 0.039 Uiso 1 1 calc R U
H22B H 0.490068 0.396606 0.474109 0.039 Uiso 1 1 calc R U
H22C H 0.565119 0.441045 0.540360 0.039 Uiso 1 1 calc R U
C23 C 0.3651(3) 0.38633(7) 0.8684(3) 0.0201(5) Uani 1 1 d . .
C24 C 0.3067(3) 0.35831(7) 0.9717(3) 0.0251(5) Uani 1 1 d . .
H24A H 0.224259 0.338586 0.904428 0.038 Uiso 1 1 calc R U
H24B H 0.253978 0.374748 1.033200 0.038 Uiso 1 1 calc R U
H24C H 0.403844 0.343296 1.045100 0.038 Uiso 1 1 calc R U
C25 C 0.4145(3) 0.42773(7) 0.9044(3) 0.0188(5) Uani 1 1 d . .
C26 C 0.4254(3) 0.45151(7) 1.0358(3) 0.0212(5) Uani 1 1 d . .
H26 H 0.393867 0.438815 1.116638 0.025 Uiso 1 1 calc R U
F1 F 0.80820(17) 0.43595(4) 1.10703(15) 0.0286(3) Uani 1 1 d . .
F2 F 1.08938(18) 0.42419(4) 1.17601(15) 0.0291(3) Uani 1 1 d . .
F3 F 0.35755(17) 0.50972(4) 0.65985(15) 0.0285(3) Uani 1 1 d . .
F4 F 0.63898(17) 0.49717(4) 0.73736(16) 0.0284(3) Uani 1 1 d . .
N1 N 0.9218(2) 0.42470(6) 0.8966(2) 0.0191(4) Uani 1 1 d . .
N2 N 1.0233(2) 0.50986(5) 0.9413(2) 0.0179(4) Uani 1 1 d . .
N3 N 0.4573(2) 0.44411(5) 0.7802(2) 0.0191(4) Uani 1 1 d . .
N4 N 0.4760(2) 0.49046(5) 1.0587(2) 0.0186(4) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
F1 B1 F2 110.19(18) . .
F1 B1 N1 113.46(19) . .
F2 B1 N1 110.41(19) . .
F1 B1 N2 107.20(18) . 3_767
F2 B1 N2 108.06(19) . 3_767
N1 B1 N2 107.29(17) . 3_767
F4 B2 F3 109.99(19) . .
F4 B2 N3 113.81(19) . .
F3 B2 N3 110.89(19) . .
F4 B2 N4 106.72(18) . 3_667
F3 B2 N4 107.49(18) . 3_667
N3 B2 N4 107.63(18) . 3_667
C2 C1 C6 120.6(2) . .
C2 C1 H1 119.7 . .
C6 C1 H1 119.7 . .
C3 C2 C1 120.9(2) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 119.4(2) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C3 C4 C5 119.9(2) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C4 C5 C6 121.4(2) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 117.8(2) . .
C5 C6 C7 121.2(2) . .
C1 C6 C7 121.1(2) . .
C10 C7 C8 107.18(19) . .
C10 C7 C6 127.3(2) . .
C8 C7 C6 125.5(2) . .
N1 C8 C7 108.85(19) . .
N1 C8 C9 121.38(19) . .
C7 C8 C9 129.8(2) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 C12 106.65(19) . .
C7 C10 C11 128.7(2) . .
C12 C10 C11 124.6(2) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 N1 120.96(19) . .
C13 C12 C10 129.8(2) . .
N1 C12 C10 109.12(19) . .
N2 C13 C12 126.1(2) . .
N2 C13 H13 117.0 . .
C12 C13 H13 117.0 . .
C15 C14 C19 120.9(2) . .
C15 C14 H14 119.6 . .
C19 C14 H14 119.6 . .
C16 C15 C14 120.4(2) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C15 C16 C17 119.7(2) . .
C15 C16 H16 120.1 . .
C17 C16 H16 120.1 . .
C16 C17 C18 120.2(2) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C19 C18 C17 120.9(2) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C18 C19 C14 117.9(2) . .
C18 C19 C20 121.2(2) . .
C14 C19 C20 120.9(2) . .
C23 C20 C21 107.02(19) . .
C23 C20 C19 127.6(2) . .
C21 C20 C19 125.3(2) . .
N3 C21 C20 109.37(19) . .
N3 C21 C22 121.5(2) . .
C20 C21 C22 129.1(2) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C23 C25 106.58(19) . .
C20 C23 C24 128.6(2) . .
C25 C23 C24 124.8(2) . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C26 C25 N3 120.70(19) . .
C26 C25 C23 130.6(2) . .
N3 C25 C23 108.68(18) . .
N4 C26 C25 125.7(2) . .
N4 C26 H26 117.2 . .
C25 C26 H26 117.2 . .
C8 N1 C12 108.19(17) . .
C8 N1 B1 129.48(18) . .
C12 N1 B1 121.78(18) . .
C13 N2 N2 117.4(2) . 3_767
C13 N2 B1 118.07(17) . 3_767
N2 N2 B1 123.8(2) 3_767 3_767
C21 N3 C25 108.34(18) . .
C21 N3 B2 128.64(18) . .
C25 N3 B2 122.35(18) . .
C26 N4 N4 117.9(2) . 3_667
C26 N4 B2 117.75(17) . 3_667
N4 N4 B2 123.7(2) 3_667 3_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.373(3) .
B1 F2 1.392(3) .
B1 N1 1.529(3) .
B1 N2 1.598(3) 3_767
B2 F4 1.376(3) .
B2 F3 1.392(3) .
B2 N3 1.518(3) .
B2 N4 1.596(3) 3_667
C1 C2 1.386(3) .
C1 C6 1.398(3) .
C1 H1 0.9500 .
C2 C3 1.380(4) .
C2 H2 0.9500 .
C3 C4 1.387(4) .
C3 H3 0.9500 .
C4 C5 1.387(3) .
C4 H4 0.9500 .
C5 C6 1.397(3) .
C5 H5 0.9500 .
C6 C7 1.485(3) .
C7 C10 1.397(3) .
C7 C8 1.421(3) .
C8 N1 1.353(3) .
C8 C9 1.494(3) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C12 1.402(3) .
C10 C11 1.501(3) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.380(3) .
C12 N1 1.386(3) .
C13 N2 1.324(3) .
C13 H13 0.9500 .
C14 C15 1.383(3) .
C14 C19 1.401(3) .
C14 H14 0.9500 .
C15 C16 1.378(4) .
C15 H15 0.9500 .
C16 C17 1.380(4) .
C16 H16 0.9500 .
C17 C18 1.391(3) .
C17 H17 0.9500 .
C18 C19 1.391(3) .
C18 H18 0.9500 .
C19 C20 1.477(3) .
C20 C23 1.406(3) .
C20 C21 1.414(3) .
C21 N3 1.349(3) .
C21 C22 1.494(3) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C25 1.408(3) .
C23 C24 1.500(3) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 C26 1.382(3) .
C25 N3 1.391(3) .
C26 N4 1.325(3) .
C26 H26 0.9500 .
N2 N2 1.402(3) 3_767
N4 N4 1.399(3) 3_667
